JP2008526818A5 - - Google Patents
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- JP2008526818A5 JP2008526818A5 JP2007549915A JP2007549915A JP2008526818A5 JP 2008526818 A5 JP2008526818 A5 JP 2008526818A5 JP 2007549915 A JP2007549915 A JP 2007549915A JP 2007549915 A JP2007549915 A JP 2007549915A JP 2008526818 A5 JP2008526818 A5 JP 2008526818A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- hydrogen
- substituted
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 47
- 239000001257 hydrogen Substances 0.000 claims 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 24
- 150000002367 halogens Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 20
- -1 nitro, amino Chemical group 0.000 claims 19
- 150000002431 hydrogen Chemical group 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 239000011737 fluorine Substances 0.000 claims 16
- 229910052731 fluorine Inorganic materials 0.000 claims 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 9
- 239000000460 chlorine Chemical group 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- HBMUMVMGBLMQJT-UHFFFAOYSA-N pyrrolo[2,1-a]isoquinoline Chemical group C12=CC=CC=C2C=CN2C1=CC=C2 HBMUMVMGBLMQJT-UHFFFAOYSA-N 0.000 claims 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 125000005605 benzo group Chemical group 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 239000001301 oxygen Chemical group 0.000 claims 8
- 239000011593 sulfur Chemical group 0.000 claims 8
- 229910052717 sulfur Chemical group 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- URBDWHWYNSSOST-UHFFFAOYSA-N C1=CNC=C2C3=CC=NC3=CC=C21 Chemical group C1=CNC=C2C3=CC=NC3=CC=C21 URBDWHWYNSSOST-UHFFFAOYSA-N 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- YNXLOPYTAAFMTN-SBUIBGKBSA-N C([C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)C1=CC=C(O)C=C1 Chemical compound C([C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)C1=CC=C(O)C=C1 YNXLOPYTAAFMTN-SBUIBGKBSA-N 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- 102000016267 Leptin Human genes 0.000 claims 1
- 108010092277 Leptin Proteins 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000016285 Movement disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 108010088847 Peptide YY Proteins 0.000 claims 1
- 102100029909 Peptide YY Human genes 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 210000000577 adipose tissue Anatomy 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000000883 anti-obesity agent Substances 0.000 claims 1
- 229940125710 antiobesity agent Drugs 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims 1
- 229960002802 bromocriptine Drugs 0.000 claims 1
- 230000007278 cognition impairment Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 229960002179 ephedrine Drugs 0.000 claims 1
- 230000035558 fertility Effects 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims 1
- 229940039781 leptin Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims 1
- 229960001243 orlistat Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 claims 1
- 229960003908 pseudoephedrine Drugs 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- JZCPYUJPEARBJL-UHFFFAOYSA-N rimonabant Chemical compound CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 claims 1
- 229960003015 rimonabant Drugs 0.000 claims 1
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 claims 1
- 229960004425 sibutramine Drugs 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05100154 | 2005-01-12 | ||
PCT/EP2006/050167 WO2006089815A1 (en) | 2005-01-12 | 2006-01-11 | Novel pyrrolodihydroisoquinolines as pde10 inhibitors |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008526818A JP2008526818A (ja) | 2008-07-24 |
JP2008526818A5 true JP2008526818A5 (es) | 2009-03-05 |
Family
ID=36097003
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007549915A Withdrawn JP2008526818A (ja) | 2005-01-12 | 2006-01-11 | Pde10インヒビターとしての新規のピロロジヒドロイソキノリン |
Country Status (9)
Country | Link |
---|---|
US (1) | US20080161338A1 (es) |
EP (1) | EP1838707B1 (es) |
JP (1) | JP2008526818A (es) |
AT (1) | ATE430148T1 (es) |
AU (1) | AU2006218054A1 (es) |
CA (1) | CA2593750A1 (es) |
DE (1) | DE602006006544D1 (es) |
ES (1) | ES2326337T3 (es) |
WO (1) | WO2006089815A1 (es) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060148840A1 (en) * | 2003-06-30 | 2006-07-06 | Altana Pharma Ag | Pyrrolodihydroisoquinolines as pde10 inhibitors |
JP2008526817A (ja) * | 2005-01-12 | 2008-07-24 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規のピロロジヒドロイソキノリン |
WO2009070583A1 (en) * | 2007-11-30 | 2009-06-04 | Wyeth | Pyrido[3,2-e]pyrazines, process for preparing the same, and their use as inhibitors of phosphodiesterase 10 |
CN101918408A (zh) | 2007-11-30 | 2010-12-15 | 惠氏有限责任公司 | 作为磷酸二酯酶10的抑制剂的芳基和杂芳基稠合的咪唑并[1,5-a]吡嗪 |
TW200944523A (en) | 2008-02-08 | 2009-11-01 | Organon Nv | (Dihydro)pyrrolo[2,1-a]isoquinolines |
CA2827724A1 (en) | 2011-02-18 | 2012-08-23 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinolinol derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
GB201117453D0 (en) * | 2011-10-10 | 2011-11-23 | Univ Dundee | Improved sperm function/activity |
WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2761358B1 (fr) * | 1997-03-27 | 1999-05-07 | Adir | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
EP1347973A1 (en) * | 2000-12-13 | 2003-10-01 | Bayer Aktiengesellschaft | Pyrrolo (2.1-a) dihydroisoquinolines and their use as phosphodiesterase 10a inhibitors |
US20030032579A1 (en) * | 2001-04-20 | 2003-02-13 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
IL149106A0 (en) * | 2001-04-20 | 2002-11-10 | Pfizer Prod Inc | Therapeutic use of selective pde10 inhibitors |
US20030018047A1 (en) * | 2001-04-20 | 2003-01-23 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
WO2003014115A1 (en) * | 2001-08-06 | 2003-02-20 | Bayer Aktiengesellschaft | 3-substituted pyrrolo (2.1-a) isoquinoline derivatives |
WO2003051877A1 (en) * | 2001-12-18 | 2003-06-26 | Bayer Corporation | 2-substituted pyrrolo[2.1-a]isoquinolines against cancer |
US20060148840A1 (en) * | 2003-06-30 | 2006-07-06 | Altana Pharma Ag | Pyrrolodihydroisoquinolines as pde10 inhibitors |
-
2006
- 2006-01-11 CA CA002593750A patent/CA2593750A1/en not_active Abandoned
- 2006-01-11 AU AU2006218054A patent/AU2006218054A1/en not_active Abandoned
- 2006-01-11 DE DE602006006544T patent/DE602006006544D1/de active Active
- 2006-01-11 WO PCT/EP2006/050167 patent/WO2006089815A1/en active Application Filing
- 2006-01-11 AT AT06701124T patent/ATE430148T1/de not_active IP Right Cessation
- 2006-01-11 US US11/794,497 patent/US20080161338A1/en not_active Abandoned
- 2006-01-11 JP JP2007549915A patent/JP2008526818A/ja not_active Withdrawn
- 2006-01-11 ES ES06701124T patent/ES2326337T3/es active Active
- 2006-01-11 EP EP06701124A patent/EP1838707B1/en active Active
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